LAUSR

We present the preparation of tert-butyldiphenylsilanes differing in one functional group. The molecular structures of the phenyl (3), methoxy (4), and amino derivatives (5) were elucidated by single-crystal X-ray diffraction analysis and their crystal packing investigated by Hirshfeld surface analysis along with 2D fingerprint plots. In the all-C derivative 3, the high symmetry dependence of the crystal packing enables a multitude of directional C(methyl)−H⋅⋅⋅C(π) interactions between the tert-butyl and phenyl groups. The methoxy derivative 4 is characterized by considerably short H⋅⋅⋅H contacts possibly resulting from pre-orienting C(aryl)−H⋅⋅⋅O and C(aryl)−H⋅⋅⋅C(π) hydrogen bonds. In the amino derivative 5, the nitrogen atom is not involved in intermolecular interactions, instead dispersive H⋅⋅⋅H contacts might become more important for the crystal cohesion. These findings once again underline the pronounced lone electron pair density transfer from the nitrogen atom towards the silicon atom.